Potassium Carbonate → 2-Benzylthioethyl 2-[4-(5-trifluoromethyl-2-pyridyloxy)-phenoxy]-propionate

HRID 615546Notes

Reaction equation

HRID 615546 reaction equation
C(=O)([O-])[O-].[K+].[K+].[OH:7][C:8]1[CH:29]=[CH:28][C:11]([O:12][CH:13]([CH3:27])[C:14]([O:16][CH2:17][CH2:18][S:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[O:15])=[CH:10][CH:9]=1.Cl[C:31]1[CH:36]=[CH:35][C:34]([C:37]([F:40])([F:39])[F:38])=[CH:33][N:32]=1>CS(C)=O>[F:38][C:37]([F:40])([F:39])[C:34]1[CH:35]=[CH:36][C:31]([O:7][C:8]2[CH:9]=[CH:10][C:11]([O:12][CH:13]([CH3:27])[C:14]([O:16][CH2:17][CH2:18][S:19][CH2:20][C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=3)=[O:15])=[CH:28][CH:29]=2)=[N:32][CH:33]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 923422-Chloro-5-(trifluoromethyl)pyridineHCID 133096292-(Benzylsulfanyl)ethyl 2-(4-hydroxyphenoxy)propanoate

Product 1

HCID 133094732-Benzylthioethyl 2-[4-(5-trifluoromethyl-2-pyridyloxy)-phenoxy]-propionateYield 76.1%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
90 °C

Procedure

15.2 g of potassium carbonate were added to a solution of 33.2 g of 2-benzylthioethyl 2-(4-hydroxyphenoxy)-propionate in 100 ml of dimethyl sulfoxide at room temperature whilst stirring. The mixture was heated to 90° C. for 1 hour with stirring. Then, 20.0 g of 2-chloro-5-trifluoromethyl-pyridine were added thereto while maintaining the temperature between 80° and 90° C. After the addition was completed, the reaction mixture was further stirred at this temperature for 2 hours, and then cooled to room temperature. Then the reaction mixture was poured into ice water and extracted with chloroform. After drying the organic phase, the chloroform was removed under reduced pressure. There were obtained 36.3 g of 2-benzylthioethyl 2-[4-(5-trifluoromethyl-2-pyridyloxy)-phenoxy]-propionate in the form of a pale yellow viscous oil. nD20 =1.5505.

Workup

  1. stirringwith stirring
  2. temperaturewhile maintaining the temperature between 80° and 90° C
  3. additionAfter the addition
  4. stirringthe reaction mixture was further stirred at this temperature for 2 hours
  5. temperaturecooled to room temperature
  6. extractionextracted with chloroform
  7. customAfter drying the organic phase
  8. customthe chloroform was removed under reduced pressure

Sources & evidence

ORD record
ord-b3fa918ebcc94a8ab61fdd8e50a288d3
Source dataset
uspto-grants-1985_02
Patent number
US04500346

Reaction notes

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